Process of making neutral oxychinolin salts.



' pressure or in a vacuum, the dioxychinoli n/ said to be obtained byboiling two n'iolecules mums STATEsEATENT curios.

LEOPOLD OSTEltMANN, OF HAMBURG, GERMANY.

IPRQCESS OF MAKING NEUTRAL OXYCHINOLIN SALTS,

To all whom it may concern:

lie it known that .l, Lnovonu OS'IERMANN, manufacturer, a citizen ottheGerman Enipire, residing; at Hamburg, Germany, have invented certain.new and useful Improvements in Processes of Making Neutral OxychinolinSalts; and I do hereby declare the following to be a full, clear, andexact description of the invention, such as will enable others skilledin the art to which it up pertains to make and use the same.

O-oxychinolin forms salts with. acids. Beilsl'ein in his Hmzdboofi: ofOi'gai'z'ic U/tcmst/y, mentions an acid oxychinolin sulfate,- (1,1l,llQl l,S() 2ll O. United States Patent No. 466,708, a neutral oxychinolinsulfate, C H N O H SO, is

of O-oxychinoliu and one molecule of-sulfuric acid in Water solution ona reflux cooler and then distilling oil the Water in a vacuum. It hasbeen found, however, that in this Wil no neutral U-oxychinolin sulfatecan be ob tained by this applicant, as O-oxychinolin is always distilledoff With steam or water, whether the process he carried on in a vacuumor at ordinary pressure. The product of the said patent as prepared bythis applicant found to be not neutral oxychinolin sulfate, but amixture of the acid oxychinolin sulfate ivith neijitral oxychinolinsulfate, out of which it was impossible to regain the pure neutraloxychinolin sulfate itself. The melt I ing point of the'product in theU. .S. patent is stated to he 17 21? 3, Whereas neutral O-oxychinolinsulfate prepared according to this process melts at 177.53".

It has been found that by dissolving 2 molecules of oxychinoli 'iiualcohol and then adding one molecule of sulfuric acid there is formed.almost immediately a precipitate which is shown by analysis to bedi-oxychinolin sulfate, that is neutral sulfate of oxychinolin. Ifthiscompound is dissolved in Water and the Water evaporated either atatmospheric sulfate is destroyed; part of oxychinolin I is evaporatedWith the Water vapor and the remainder is a mixture of acid sulfate ofoxychinolin, With more. 0;: less undestroyed residues of the neutralsalt. In consequence of this it has been found that the neutral sulfateof oxychinolin (dhoxychinolin sulfate) is destroyed by the presence ofWater,

' Specification of Let'bem Patent. I Application filed May 25, 1906.Serial No. 318,762.

Patented-Dec. 15, 1908.

(Specimens) dissociating into oxychinoliu and the acid sulfate ofoxychinolln (mono O-oxyclnnohn sulfate) so that out of a Water solutiona part of the oxyclnnohn may be separated by distillation or b extractinr it with ether or benzol. It results that di-oxychinolin sulfate canonly he produced in the absence of Water, alcohol, for example, beingused as solvent.

v I, Di-oxychinolin sulfate has great value an antiseptic and it is anecessity of modern progress that such remedies should he prepared in anabsolutely constant and. pure form. In this respect the above describedAccording to the process is a great technical improvement and it alsoproduces a product hitherto unknown. This product differs from theproduct of said U. S. Patent No. 466,708, not only in its analysis andhigher melting point, 177.59, but also in its physical appearance andtechnical properties. it is a very finecrystalline powd' r which iseminently fitted to be formed into tablets. It is, however, nothygroscopic like the product of the said patent, Which consists of amixture of two different oxychinolin salts.

Example: Neutral o'a ychinoln Slllfffi-- 10.6 parts of sulfuric acid of65.5? Bunnie, parts of oxychinolin and 100 parts of alcohol of 96% aremixed. together. Theneutral sulfate of oxychinolin crystallizesinnnediately by cooling when left in a room the ordinary temperature.Evaporation of the dissolving fluid isnot permitted to take place. Theproduct separated from the fluid by any suitable means, as for instance,a filter press, and dried a not toov high temperature, or C. forexample. The

yiegl is the theoretical quantity less four or ve per cent. Which remaindissolved in the alcohol. The neutral oxychlnolln sulfate of thecomposition. (C l-LNG).ZH SO isa beautifully yellow crystalline powder,which is not hygroscopic, can readily be formed into tablets, is veryeasily soluble in Water,

slightly less so in alcohol and entirely insoluble in absolute ether.Its melting point is 177.5", by which it easily is distinguished frommixtures of acid sulfate of oxychinolin, Whose melting point is about172.

Neutral oxychinolin sulfate prepared in the manner above described isneither, as was assumed hitherto, a molecular mixture of freeoxychinolin with welllrnown acid exactly one. molecule of oxyehinolincan be .wit-l-ulrawn from these salts from water solution by suchextracting means other, benxin, etc. or by means of a steam jet. If,however, the dry salt is treated with other free from water, or henzinfree from waler- (mll of which is n solvent'fei oxyehinollll--llltlhitis impossible to withdraw oxyehinoliu from the salt. It followstherefore that in the present case there is pronlueecl a genuine neutraloRy -l'iinolin salt which, in water solution,*(lisassoeiates into:l(fi(l oxychinolin salt amt free oxychinolin. From the two inolerulesbtoxyehiuoliu taken up,

eeeew I claim:--

l. The process of manufacturing neutral sulfate of oxyehinolin(cli-oxyehinolin sulfate) which consists in mixing together sulfuricacid and the corresponding molecular quant ity ol' oxyehiuolin,dissolving the same in aleohol and allowing the neutral sulfate ofoxy'ehinolin to crystallize out, substantially as (iOSCllbGtl.

The process of n'lanufaeturing neutral sulfate of oxyehinolin(di-oxyehinolin sulfate) which consists in mixing together 10.6 parts ofsulfuric acid of 65.5" Bnumkand 29 parts of oxyrhinolin in 100 parts of96% alcohol and allowing the neutral sulfate of oxychinolin toCrystalline out substantially as described.

In testimony whereof, I have aflixed my signature, in presence of twowitnesses.

LEOPOLD ()STERMANN. Witnesses JOHN F. SUIIR, I. CHRIST. HAFERMANN.

